4-Methylmorpholine → HCID 178500944, compound

HRID 350897Notes

Reaction equation

Br.[C:2]([S:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)(=[NH:4])[CH3:3].CN1[CH2:23][CH2:22][O:21][CH2:20]C1.CC(C(Cl)=O)[C:26](Cl)=[O:27].C1C[O:35]CC1>O>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[CH2:6][S:5]/[C:2](=[N:4]\[C:26](=[O:27])[CH2:23][C:22]([O:21][CH3:20])=[O:35])/[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 2-naphthylmethyl ethanimidothioate hydrobromide (3.0 g, 0.01 mol) in THF (20.0 mL) at 0° C., is added N-methylmorpholine (2.4 mL. 0.022 mol), followed by the dropwise addition of a solution of methyl malonyl chloride (1.2 mL, 0.011 mol) in THF (5.0 mL). The resulting mixture is stirred at 0° C. for 30 min, and at room temperature for an additional 30 min. The mixture is diluted with cold water, (25 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts are washed with water, dried (Na2SO4), filtered and concentrated to dryness under reduced pressure to give a yellow syrup, which is purified by flash chromatography using 25% EtOAc in hexanes to give the title compound (1.9 g, 59%) as colorless syrup: ES-HR MS m/z 316.0993(M+H calcd for C17H18NO3SN requires 316.1002).

Workup

waitat room temperature for an additional 30 min
extractionextracted with dichloromethane (2×20 mL)
washThe combined organic extracts are washed with water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customto give a yellow syrup, which
customis purified by flash chromatography

Sources & evidence

ORD record: ord-43d2f06350294ed7a138440d80c7282c
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183287B2

Reaction notes

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